Acetylene-Substituted Phosphane Oxides: Building Blocks for Macrocycles
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Publication date
2007
Authors
Assema, S.G.A.
de Jong, G.B.
Ehlers, A.W.
de Kanter, F.J.J.
Schakel, M.
Spek, Anthony Louis
Lutz, Martin
Lammertsma, K.
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Abstract
Phosphorus-based macrocycles with acetylenic scaffolds have been built from acetylene-substituted phosphane oxides that were formed from diisopropylphosphoramidic dibromide (3) and an acetylenic Grignard reagent. The fourand six-edged macrocycles 15 and 16, in which the iPr2NP(O) units are connected through 1,3-butadiyne rods, were obtained from the monosilylated derivative of iPr2NP(O)(C2H)2 (7) by multiple acetylene coupling reactions under oxidative Hay conditions. Reaction of iPr2NP(O)(Br)2 (3) with lithiated 1,2-diethynylbenzene gave a mixture of cis and trans monocyclic bis(phosphane oxide) 18. An X-ray crystal structure determination of the trans isomer shows the ring structure to adopt a puckered form.
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Assema, S G A, de Jong, G B, Ehlers, A W, de Kanter, F J J, Schakel, M, Spek, A L, Lutz, M & Lammertsma, K 2007, 'Acetylene-Substituted Phosphane Oxides: Building Blocks for Macrocycles', European Journal of Organic Chemistry, pp. 2405-2412.